Which airlines fly to Chicago?

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Region of Ontario according to our data. Air Canada is the first choice among our users, with 53% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How long does it take to fly to Chicago?

Flight times from Region of Ontario to Chicago vary, but if you’re flying out of Ottawa and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 2h 19m on average. Another popular route from Region of Ontario to Chicago is flying from Toronto to Chicago O'Hare Intl Airport, which will take roughly 5h 08m. Keep in mind that layovers or delays could extend your travel time.

What is the cheapest airline that flies from Ontario to Chicago?

Porter Airlines, Air Canada, and Delta are the most popular carriers operating from Ontario to Chicago

How many flights depart from Region of Ontario to Chicago on average per week?

780 flights are operational weekly from Region of Ontario to Chicago as of July 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

How many flights depart from Region of Ontario to Chicago on average per day?

111 flights are operational daily from Region of Ontario to Chicago as of July 2026. The most popular departure time for this route is 1:00p.m., with 44% of flights per day taking off at noon.

When did momondo last update prices for flights from Ontario to Chicago?

Prices for flights from Ontario to Chicago were last updated today.

How many operators does momondo search for flights from Ontario to Chicago?

There are 5 operators available for flights from Ontario to Chicago as of July 2026.

How old do you have to be to fly from Ontario to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

C$ 192 Cheap Flights from Ontario to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Ontario to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:00 p.m. - 8:12 p.m.

YYZ

ORD

5h 12m

1 stop

3:45 p.m. - 6:30 p.m.

ORD

YYZ

1h 45mdirect

C$ 289Air Canada

Wed, 9 Sep - Wed, 16 Sep

4:00 p.m. - 8:12 p.m.

YYZ

ORD

5h 12m

1 stop

9:55 a.m. - 12:40 p.m.

ORD

YYZ

1h 45mdirect

C$ 289Air Canada

Wed, 9 Sep - Wed, 16 Sep

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 291Porter Airlines

Mon, 31 Aug - Mon, 21 Sep

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

11:45 a.m. - 2:25 p.m.

MDW

YTZ

1h 40mdirect

C$ 292Porter Airlines

Tue, 25 Aug - Wed, 9 Sep

8:50 a.m. - 9:53 a.m.

YYZ

ORD

2h 03mdirect

9:18 p.m. - 11:59 p.m.

ORD

YYZ

1h 41mdirect

C$ 295United Airlines

Fri, 4 Sep - Tue, 8 Sep

5:15 p.m. - 6:30 p.m.

YYZ

ORD

2h 15mdirect

8:50 a.m. - 11:49 a.m.

ORD

YYZ

1h 59mdirect

C$ 295United Airlines

Thu, 24 Sep - Sun, 27 Sep

5:15 p.m. - 6:30 p.m.

YYZ

ORD

2h 15mdirect

8:40 p.m. - 11:26 p.m.

ORD

YYZ

1h 46mdirect

C$ 295Multiple Airlines

Thu, 24 Sep - Sun, 27 Sep

2:45 p.m. - 3:51 p.m.

YYZ

ORD

2h 06mdirect

2:15 p.m. - 5:01 p.m.

ORD

YYZ

1h 46mdirect

C$ 295Multiple Airlines

Wed, 16 Sep - Thu, 17 Sep

7:15 p.m. - 8:20 p.m.

YYZ

ORD

2h 05mdirect

8:03 a.m. - 10:59 a.m.

ORD

YYZ

1h 56mdirect

C$ 296American Airlines

Fri, 11 Sep - Sun, 13 Sep

7:20 a.m. - 8:30 a.m.

YYZ

ORD

2h 10mdirect

10:35 a.m. - 4:45 p.m.

ORD

YYZ

5h 10m

1 stop

C$ 309American Airlines

Wed, 2 Sep - Wed, 9 Sep

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American Airlines flights from Region of Ontario to Chicago

Our best American Airlines deals on Region of Ontario to Chicago flight tickets

American Airlines

12 Aug

YYZ6:15 a.m.Toronto Pearson Intl

5h 36m

1 stop

ORD10:51 a.m.Chicago O'Hare Intl

19 Aug

ORD4:00 p.m.Chicago O'Hare Intl

6h 46m

1 stop

YYZ11:46 p.m.Toronto Pearson Intl

C$ 477

American Airlines

11 Aug

YYZ11:01 a.m.Toronto Pearson Intl

7h 13m

1 stop

ORD5:14 p.m.Chicago O'Hare Intl

16 Aug

ORD8:09 a.m.Chicago O'Hare Intl

1h 50m

YYZ10:59 a.m.Toronto Pearson Intl

C$ 492

American Airlines

5 Aug

YUL12:30 p.m.Montreal Pierre Elliott Trudeau Intl

2h 39m

ORD2:09 p.m.Chicago O'Hare Intl

12 Aug

ORD8:18 a.m.Chicago O'Hare Intl

2h 25m

YUL11:43 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 518

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

Air Canada

9 Sep

YYZ4:00 p.m.Toronto Pearson Intl

5h 12m

1 stop

ORD8:12 p.m.Chicago O'Hare Intl

16 Sep

ORD3:45 p.m.Chicago O'Hare Intl

1h 45m

YYZ6:30 p.m.Toronto Pearson Intl

C$ 289

Air Canada

23 Sep

YTZ12:15 p.m.Toronto Island

2h 06m

ORD1:21 p.m.Chicago O'Hare Intl

27 Sep

ORD2:00 p.m.Chicago O'Hare Intl

1h 42m

YTZ4:42 p.m.Toronto Island

C$ 291

Air Canada

17 Sep

YTZ7:35 p.m.Toronto Island

2h 06m

ORD8:41 p.m.Chicago O'Hare Intl

22 Sep

ORD8:45 a.m.Chicago O'Hare Intl

6h 05m

1 stop

YTZ3:50 p.m.Toronto Island

C$ 292

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/9

4:00 p.m.-8:12 p.m.

1 stop5h 12m

Chicago O'Hare Intl

Wed 16/9

3:45 p.m.-6:30 p.m.

Nonstop1h 45m

C$ 289

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/9

4:00 p.m.-8:12 p.m.

1 stop5h 12m

Chicago O'Hare Intl

Wed 16/9

9:55 a.m.-12:40 p.m.

Nonstop1h 45m

C$ 289

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 31/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 21/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 291

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 9/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 292

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 4/9

8:50 a.m.-9:53 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Tue 8/9

9:18 p.m.-11:59 p.m.

Nonstop1h 41m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 24/9

5:15 p.m.-6:30 p.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sun 27/9

8:50 a.m.-11:49 a.m.

Nonstop1h 59m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 24/9

5:15 p.m.-6:30 p.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sun 27/9

8:40 p.m.-11:26 p.m.

Nonstop1h 46m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 16/9

2:45 p.m.-3:51 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Thu 17/9

2:15 p.m.-5:01 p.m.

Nonstop1h 46m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/9

7:15 p.m.-8:20 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 13/9

8:03 a.m.-10:59 a.m.

Nonstop1h 56m

C$ 296

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 2/9

7:20 a.m.-8:30 a.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 9/9

10:35 a.m.-4:45 p.m.

1 stop5h 10m

C$ 309

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Region of Ontario to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of September is another great option to travel to Chicago, with average flight prices from Region of Ontario averaging around C$ 370.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 632. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 999. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the morning is the cheapest time of day to fly from Region of Ontario to Chicago when you can find flight prices for as low as C$ 698. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,066 per ticket.

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago flight prices

How far in advance should I book a flight from Ontario to Chicago?

You are more likely to see cheaper flights to Chicago from Region of Ontario when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 430 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Region of Ontario for as low as C$ 247 on momondo.

What cabin class options are available on Region of Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Region of Ontario to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Region of Ontario to Chicago flights?

You could potentially save up to 3% on your flight if you consider stops on a Region of Ontario to Chicago flight.

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best price found	C$ 182
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Region of Ontario in the past 72 hours is C$ 182. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is C$ 289.

The fastest flight from Region of Ontario to Chicago takes 1h 50m

Direct flights go from Region of Ontario to Chicago every day.

There are 3 airports in Chicago. From Region of Ontario there are direct flights to Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Ontario to Chicago

When did momondo last update prices for flights from Ontario to Chicago?
Prices for flights from Ontario to Chicago were last updated today.
How many operators does momondo search for flights from Ontario to Chicago?
There are 5 operators available for flights from Ontario to Chicago as of July 2026.
How old do you have to be to fly from Ontario to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Region of Ontario to Chicago?
Based on momondo bookings for flights between Region of Ontario and Chicago, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 21.66% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 10.09%, Boeing 737-800 with 10.06%, and Boeing 737-900 with 8.31%.

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 201	Free Cancellation	Rating 8.0 449 reviews	Search Porter Airlines flights
American Airlines	PriceFrom C$ 255	Free Cancellation	Rating 7.1 11,839 reviews	Search American Airlines flights
Air Canada	PriceFrom C$ 278	Free Cancellation	Rating 7.1 11,405 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 278	Free Cancellation	Rating 7.4 10,052 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 377	Free Cancellation	Rating 7.2 3,415 reviews	Search WestJet flights

Merrillville

Hammond

Munster

Valparaiso

Portage

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

Finding the right flight to Chicago from Ontario is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

Flights from Ontario to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Ontario to Chicago?

Once all potential Ontario to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Ontario and alert you when they change.

An easier way to manage your Chicago trip

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Fly into one of these airports located in Chicago

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Cheap flights from Ontario to Chicago from C$ 192

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Ontario to Chicago departing on 26/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Region of Ontario to Chicago

Our best American Airlines deals on Region of Ontario to Chicago flight tickets

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

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How to get the cheapest flight ticket from Region of Ontario to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Ontario to Chicago flight route?

How far in advance should I book a flight from Ontario to Chicago?

What cabin class options are available on Region of Ontario to Chicago flights?

Can stopping save me money on Region of Ontario to Chicago flights?

What is the cheapest airline that flies from Ontario to Chicago?

Which airlines fly to Chicago?

How many flights depart from Region of Ontario to Chicago on average per day?

How many flights depart from Region of Ontario to Chicago on average per week?

How long does it take to fly to Chicago?

Cheap Region of Ontario to Chicago flight deals and tips

Best price found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Ontario to Chicago

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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